Hydrochloric Acid → 4-(2-Fluoro-6-(trifluoromethyl)phenyl)piperidine Hydrochloride

HRID 58432Notes

Reaction equation

HRID 58432 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1.[ClH:25]>C(Cl)Cl.CCOCC>[ClH:25].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[C:3]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483502HCID 118483502, compound

Product 1

HCID 1184834834-(2-Fluoro-6-(trifluoromethyl)phenyl)piperidine Hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-fluoro-6-(trifluoromethyl)phenyl)piperidine-1-carboxylate (22, 0.219 g, 0.63 mmol) in CH2Cl2 (4 mL) was added 2 N HCl (2.0 N solution in Et2O, 4 mL), and the mixture was stirred at ambient temperature for 4 h. The reaction mixture was diluted with Et2O (50 mL) and the solids were collected by filtration to give 4-(2-fluoro-6-(trifluoromethyl)phenyl)piperidine hydrochloride (23) as an offwhite solid (158 mg, 88%): 1H NMR (300 MHz, DMSO-d6) δ 8.82 (br s, 1H), 8.50 (br s, 1H), 7.66-7.48 (m, 3H), 3.42-3.33 (m, 2H), 3.24-2.95 (m, 3H), 2.35-2.15 (m, 2H), 1.87-1.74 (m, 2H); ESI MS m/z 248 [M+H]+.

Workup

  1. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-44e998b2774346a0bd1a52455d02730e
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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